New cotton dyestuffs and process of making same.



No Drawing.

UNITED STATES PATENT" RICHARD GAST, or FECHENHEIM, NEARrRAiiKFoRT-oii-THs MAIn} GERitIANY, AS-

; SIGNOR 'rp CASSELLA COLOR COMPANY, or NEW YORK, N. Y.

7T0 all 'wlwni z't'mag concern:

e it known that-I. Rlcimuo (ias'r, doctor P sophy, a subject of theDuchy of Anhalt; in the German lhupiregand a resident of()fi'cnbacherlandstrasc (i0, Fccheuhelm, near Frankfort-o1i-thc-Mam, Gen

. 'many, have invented some New Cotton D e '-"st-ufi's and a Process ofMaking Same, of

which the-"following is a full description.

' t I hare discovered that the hitherto unknownformylarylan'rinonaphthol sultou ic -acids may be obtained with ease byboilmg the: alkaline salts of the ar \'lainino- *naphthol sulfonic acidswith formic acid.

hydrogen atom.

The new foi'mylarylam'inonaphthol sulfonic acids are formed according tothe equation con NHaryl N C H OH aryl s0,H+nc0on-cmii. on+n- -o X S03"in which X represents a sult'o group or a The new acids aredistinguished from the starting materials by their greater solubilityand by their property not. to forni-nitrosamins. The azo dyestntl'sderived from the new acids are distinguished by their brilliant shadesand their fastness to acids and light. Their constitution is representedby the general formula cou nryl R-N-N-CmH. on

SOaNiL in which R signifies an aromatic radical which X signifies asulfo group or a hydrogen atom.

" The production of the new acids and dye- NEWf COTTON DYESiTUFFS ANDP'RocEssbF' MAKING sAME.

Specification of Letters Patent. Patented lugi 1912, Application filedJune 24, 1910. serial No. 568,640.

stufl's" is illustrated by the following examples. v

Example I: By heating phenyl-2.5-amin0- m\phthol-T.sultonic acid in anaqueous solution with sodium formate the formylphenyl-2.5-aminonaphthol-T-sulfohic acid is formed,

lu carrying the invention into effect in practice 94.5 kilos phenyl-2.5-ami n0naphthol-T-sulforiic acid are heatedg toboihng point with 500kilos 85 per cent. formic acid and :45 kilos for-mate of soda. Gomplcte.solution sets in after a quarter of an hour and the greater part will bythenbe found to be formylated. Boiling is then continued for anotherhour and a half and the solution is poured into salt water of 24 degrees136. preferably after hailing distilled otl anyexcess of formic acid.The formyl compound separates as a resin and congeals after some time toa whitish-gray mass which is.filtered off and washed with salt water.The yield is almost quantitative.

The sodium salt and the free acid dissolve easily in a little coldwater. The sodium salt is soluble in hot alcohol and separates again oncooling. After protracted standing in concentrated cold aqueoussolutions it The formyl separates in a crystalline form. acid thusobtained yields es ially valuable coloring matters if combined withdiazoazo compounds.

Example II: The aminoazo body obtained by diazotizing 17.3 kilossulfanilic acid and coupling with 12.1 kilos p-xylidin is dissolved as asodium salt; and di' tized with (3.9 kilos nitrite of soda and 61 kiloshydrochloric acid. The diazo compound is drawn off by suction, washed,and run into a solution of 36.5 kilos 'formylphenyl-2.5.7-

aminonaphthol sulfonic acid made alkaline by the addition'of carbonateof soda. The

ing to 35 C., the suspended dyestutf is salted out and filtered, oil. Itdissolves in water with a claret-red color which is not changed by theaddition of dilute hydrocoupling'takes place very soon. Afterheatsdin-o-sulfonic acid, and coupling with 12.1

kilos p-xylidin istransformed by soda. lye

' a into the sodium salt,-a.nd diazotized at-0 C.;with 6.9 kilos nitriteofsoda and 61 kilos hydrochloric acid. This operation being complete,the diazo compound is salted out, -:filtered off, and washed. It 'isthen run into. a solution-of 36.5' kilos formyl'phenyl-2.5.7-aminonaphthol sulfonic' acid; charged.

with an excess ofcarbonate of soda. The dystufl separates, is salted outafter heating-'the' solution, and filteredofi'. It dyes cotton -violetshades, dissolves in waterwith a reddish-violet color and thi" solutionis hardly changed by dilute hydrochloric acid.

Example IV: The diazo compound obtained from 31.9 kilos aminonaphtholdisulfonic acid 1.8.3.6 is filtered ofi,.washed, and charged 'with asolution 0t 13.7 kilos maminocresolmethylether in '13 kilos hydrochloricacid. In-order to accelerate the coupling, 27 kilos acetate of :soda areadded. The following day the whole is acidulated with 13 kiloshydrochloricv acid, salted out, and filtered The aminoazo bodyobtainedin this manner is dissolved with 24 kilos soda he in 250 literswater, and diazo- .tized with 7.2 kilosnitrite of soda and 61 kiloshydrochloric acid. This diazotizing solution is introduced into asolution of 38.3 .kilos sodium salt of the formylphenyl-2.5.7-aminonaphthol sulfonic' acid, charged with-64 kilos carbonate ofsoda. The coupling is complete after a short while. It is then" heatedto 60, C., precipitated with common salt, and filtered off. Thedyestufi' dyes cotton reddish-blue shades. It dissolv'es in water with apurple color which is turned slightly redder bydilute hydrochloric acid.

Having now particularly described and ascertained the nature of my saidinvention "and in what'manner the same is to be performed, ,I declarethat what I claim is 1. The process of producing azo coloring matters bytreating arylaminonaphthol sulfonic acids with formic acid and combiningthe products thus obtained with diazoazo compounds.

. 2. The coloring matter. derived from a dia-z azo compound andformylarylaminonap tholsulfonic acid 2.5.7 which is easily soluble inwater with claret to purple shades dyeing from such solution unmordentedcotton violet to bluish shades, which yields on being reduced by zincdust and acids formylaryldiaminonaphthol sulfonic acid and which doesnot react with nitrous acid, substantially as described.

In "witness whereof I have hereunto signed my name this 8th day of June1910, in the presence of two subscribing witnesses.

RICHARD GA ST.

